The Night of My Life

I live in England, and am leaving school this year, and am 18 years old. We've adopted the American tradition of prom, where guys get tuxedos and girls get dresses, and they all go to a party and dance with each other. The prom was in July, and when my story began it was May.

People were beginning to ask people to go with them to prom. A few people had girlfriends or boyfriends, and others just went as friends. There was one guy called Joe. He is 6 feet tall, got blonde hair and is the captain of the rugby team. Despite his godly appearance, girls hated him. He was a complete dick to them and others in our year, and he had a bad reputation. It was obvious nobody was going to go with him.

I'm gay, and have been crossdressing since I was 12. It had always been my dream to wear the big prom dress and take a hunk with me, for that slow dance to kiss to, and to let fuck me afterwards.

Joe had realised nobody was going to go with him, so I asked him the usual stuff - "Have you asked anyone yet?"... "Got your eye on anyone?"... and so on, and it was clear he was suspicious about my intentions. After about a week of flirting with him, he asked me if I was gay, and if I wanted to go to prom with him.

I was over the moon. I went out and bought the lot - sexy red lingerie, fake tits, beautiful pink dress. My sister took me to all the shops, and trying the dress on was one of the best feelings. We'd got to a department store, and the male attendants in there were so camp. They loved helping me, and there was one really hot one. He wouldn't have looked out of place in a premiership football team, but his voice and camp mannerisms gave away the fact he was gay. He picked out a gorgeous dress, and helped me try it on. My sister was impressed, if not a little jealous, at how good I looked in it. She helped me get ready on the night too, doing my make up, getting the wig right, tucking my dick away, even giving me some condoms. My parents were, to say the least, disappointed that I was being taken to the prom as a girl, rather than taking a girl myself, but they did their best to respect my decision.

Joe turned up at my door grinning, and, after saying bye to my parents, we shared our fist kiss of the night. He had his hands around my waist, I had mine around his neck. It was such an intimate moment, I never wanted it to end. It did, and we got in the limo he'd hired and went to prom.

We both got the funny looks. People knew it was me, and that we were both gay. Some of my "friends", in shock, didn't speak to me, but several of my girl friends commented on how pretty I looked, and how it was brave.

We had our dance, again sharing another kiss, and I could feel his erection grinding up to my cleverly tucked away bulge. I told him to calm down, and to save it for tonight.

We went to a party afterwards. After a few more alcoholic drinks, people didn't care about who I was, and I shared a few sexy dances with a couple of hot guys. Joe didn't mind, as he dancing with some girls he'd not met before too. I saw him make out with a blonde girl, so I thought I'd take advantage of the hot guy on the couch, who was absolutely wasted. I just sat down next to him, and started making out with him, fondling his dick a bit. Sober, he wouldn't have looked twice at a transvestite girl, but in the state he was in, he didn't care.

Joe came over, jealously, and tore me off him, carrying me up to a room upstairs, and laying me down on the bed. He tore open a condom, lubed it up and fucked my virgin arse. I was crying by the end of it, but it was so worth it to see his face. We laid on the bed for about 20 minutes, as I got over the recent fucking, and he kissed my neck caressingly, before another couple came in for a shag. The best night of my life.